(5-氨基戊基)(苯基甲氧基)氨基甲酸叔丁酯 | 129245-21-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (5-氨基戊基)(苯基甲氧基)氨基甲酸叔丁酯
• 中文别名: 甲磺酸去铁敏中间体2；(5-氨基戊基)(苯基甲氧基)氨基甲酸1,1-二甲基乙酯
• 英文名称: N-(5-aminopentyl)-N-(tert-butoxycarbonyl)-O-benzylhydroxylamine
• 英文别名: O-benzyl-N-(5-aminopentyl)-N-(tert-butoxycarbonyl)hydroxylamine；(5-Aminopentyl)(phenylmethoxy)carbamic acid tert-butyl ester；tert-butyl N-(5-aminopentyl)-N-phenylmethoxycarbamate
• CAS: 129245-21-2
• 化学式: C₁₇H₂₈N₂O₃
• 分子量: 308.421
• InChiKey: DHJOLNKVLZRNGD-UHFFFAOYSA-N

物化性质

• 沸点：
  423.6±38.0 °C(Predicted)
• 密度：
  1.057
• 溶解度：
  可溶于二氯甲烷、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  64.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5-氨基戊基)(苯基甲氧基)氨基甲酸叔丁酯 在 palladium on activated charcoal 吡啶 、 氢气 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 25.0~81.0 ℃ 、101.33 kPa 条件下， 反应 93.33h， 生成 1-(tert-Butoxycarbonyl)-7,18,29-trihydroxy-8,11,19,22,30-pentaoxo-1,7,12,18,23,29-hexaazahentriacontane
  参考文献：
  名称：

  A Versatile Synthesis of Deferrioxamine B

  摘要：

  A new and versatile route to N'-[5-[[4-[[5-(acetylhydroxyamino)pentyl]amino]-1,4-dioxobutyl]-hydroxyamino]pentyl]-N-(5-aminopentyl)-N-hydroxybutanediamide, deferrioxamine B (DFO), is described. The key improvement over the two prior routes was replacement of the nitrile in 2 with a tert-butoxycarbonyl-protected amino terminus. Elimination of the nitrile improved the kinetics of hydrogenation in that the benzyl groups of 12 were cleaved more rapidly than saturation of the cyano group of 2, and a potential overreduction byproduct (4) was thus avoided. N-(Benzyloxy)-1,5-diaminopentane (6) was selectively protected at the primary amino site with a tert-butoxycarbonyl (BOG) group, providing 7. This was reacted at the (benzyloxy)amine with succinic anhydride to produce carboxylic acid 8, which was in turn acylated regiospecifically with diamine 6 at the primary amine to give (benzyloxy)amine 9. The previous two steps were reiterated to afford DFO reagent 11. This synthon allows for modification of DFO at either end of the molecule, thus providing more flexibility in accessing DFO analogues than any prior route. Acetylation of TI, followed by hydrogenolysis and tert-butoxycarbonyl group removal, furnished DFO.

  DOI：

  10.1021/jo00106a022
• 作为产物：
  描述：

  5-氯戊腈 在 镍 ammonium hydroxide 、 sodium hydride 、 sodium iodide 作用下， 以 甲醇 为溶剂， 85.0 ℃ 、399.9 kPa 条件下， 反应 7.75h， 生成 (5-氨基戊基)(苯基甲氧基)氨基甲酸叔丁酯
  参考文献：
  名称：

  比沙卡伯林的总合成

  摘要：

  介绍了6,17-二羟基-1,6,12,17-四氮杂环二十二烷-2,5,13,​​16-四氢呋喃（比沙卡伯林）的第一个全合成。这项研究中使用的合成方案说明了O-苄基-N-（叔丁氧基羰基）-N-（4-氰基丁基）羟胺3的用途，它是合成双花青素和去铁胺B的中间体。双花青素大环内酰胺利用一系列连续的酰化和腈还原反应，由中间体3和O-苄基-N-（4-氰基丁基）羟胺4构成线性前体，即线性ω-氨基酸10。10的环化生成22元环6,17-二苄基双卡布巴林11。在最后一步中，异羟肟酸酯的脱保护得到了天然产物布卡巴林1。

  DOI：

  10.1016/s0040-4020(01)81074-7

文献信息

• [EN] ANTIBACTERIAL SIDEROMYCINS<br/>[FR] SIDÉROMYCINES ANTIBACTÉRIENNES
  申请人：MILLER MARVIN J

  公开号：WO2016027262A1

  公开（公告）日：2016-02-25

  A compound, comprising: an Fe(III)-binding and/or Fe(III)-bound siderophore; one or more optional linker covalently bound to the siderophore; and daptomycin covalently bound to the linker, or, if no linker is present, then to the siderophore; or pharmaceutically acceptable salt or solvate thereof.

  一种化合物，包括：与Fe(III)结合和/或Fe(III)结合的铁载体；一个或多个可选的与铁载体共价结合的连接剂；以及共价结合到连接剂的达托霉素，或者如果没有连接剂存在，则共价结合到铁载体；或其药用可接受的盐或溶剂。
• Forward and Reverse (Retro) Iron(III) or Gallium(III) Desferrioxamine E and Ring-Expanded Analogues Prepared Using Metal-Templated Synthesis from <i>endo</i>-Hydroxamic Acid Monomers
  作者：Tulip Lifa、William Tieu、Rosalie K. Hocking、Rachel Codd

  DOI：10.1021/acs.inorgchem.5b00141

  日期：2015.4.6

  preorganize the forward endo-hydroxamic acid monomer 4-[(5-aminopentyl)(hydroxy)amino]-4-oxobutanoic acid (for-PBH) about iron(III) in a 1:3 metal/ligand ratio to furnish the iron(III) siderophore for-[Fe(DFOE)] (ferrioxamine E) following peptide coupling. Substitution of for-PBH with the reverse (retro) hydroxamic acid analogue 3-(6-amino-N-hydroxyhexanamido)propanoic acid (ret-PBH) furnished ret-[Fe(DFOE)]

  一种金属模板合成（MTS）方法用于preorganize正向内-hydroxamic酸单体4 - [（5-氨基戊基）（羟基）氨基] -4-氧代丁酸（用于在约铁（III）-PBH）肽偶联后，金属/配体比率为1：3，可为-[Fe（DFOE）]（铁氧胺E）提供铁（III）铁载体。取代为-PBH与反向（逆）异羟肟酸类似物3-（6-氨基- ñ -hydroxyhexanamido）丙酸（RET -PBH）布置RET - [Fe（上DFOE）]（RET -ferrioxamine E）。作为异构体，对- [Fe（上DFOE）]和RET - [Fe（上DFOE）〕得到相同质谱信号（[M + H+ ] +，米/ Ž计算值654.3，米/ Ž OBS 654.3），但为- [Fe（上DFOE）〕洗脱以更极性窗口（吨- [R = 23.44分钟）比保留- [Fe（上DFOE）]（吨R = 28.13分钟）在C
• Design, Synthesis and Evaluation of AdSS Bisubstrate Inhibitors
  作者：Nidhi Tibrewal、Gregory I. Elliott

  DOI：10.1002/cmdc.202000498

  日期：2020.12.3

  Many cancers lack the expression of methylthioadenosine phosphorylase (MTAP). These cancers require adenylosuccinate synthetase (AdSS) for nucleic acid synthesis. By inhibiting adenylosuccinate synthetase, we potentially have a new therapeutic agent. Bisubstrate inhibitors were synthesized and evaluated against purified AdSS. The best activity was obtained with adenosine bearing a four‐carbon linker

  许多癌症缺乏甲基硫腺苷磷酸化酶 (MTAP) 的表达。这些癌症需要腺苷酸琥珀酸合成酶 (AdSS) 来合成核酸。通过抑制腺苷酸琥珀酸合成酶，我们有可能获得一种新的治疗剂。合成双底物抑制剂并针对纯化的 AdSS 进行评估。使用带有将N-甲酰基-N-羟基部分连接到嘌呤核苷的 6 位的四碳接头的腺苷获得了最佳活性。
• Synthesis and biological evaluation of hydroxamate-based iron chelators
  作者：Raymond J. Bergeron、Jan Wiegand、James S. McManis、P. Thirumalai Perumal

  DOI：10.1021/jm00115a006

  日期：1991.11

  desferrioxamine B (DFO, 1) is described. Hydroxamate reagent 4 was elaborated in a series of high yield steps to the tert-butoxycarbonyl nitrile 11, which provided DFO in three transformations. The intermediate 11 could also be utilized in the preparation of DFO analogues which contain terminal N-acyl groups other than acetyl. The methodology was further employed in the syntheses of the DFO polyether analogues 2

  描述了一种去铁胺X（DFO，1）的新型通用途径。用一系列高产率的步骤将异羟肟酸酯试剂4精制到叔丁氧羰基腈11上，该叔丁氧羰基腈11可通过三个转化提供DFO。中间体11也可以用于制备含有除乙酰基以外的末端N-酰基的DFO类似物。从N-（叔丁氧羰基）-O-苄基羟胺的3,6,9-三氧羰基化开始，该方法进一步用于DFO聚醚类似物2和3的合成中。聚醚2和3是中性分子，比母体DFO亲脂性更高。聚醚异羟肟酸酯2在清除大鼠铁中的功效是去铁胺的近3倍。
• [EN] MULTIDENTATE BIFUNCTIONAL CHELATING AGENTS FOR RADIONUCLIDE COMPLEXATION IN DIAGNOSTICS AND THERAPY<br/>[FR] AGENTS BIFONCTIONNELS MULTIDENTATES DE CHÉLATION POUR LA COMPLEXATION DE RADIONUCLÉIDES EN DIAGNOSTIC ET EN THÉRAPIE
  申请人：UNIV ZUERICH

  公开号：WO2015140212A1

  公开（公告）日：2015-09-24

  The invention relates to octadentate ligands of a general formula R1 - D - X - D - X - D - X - D - E - R2, wherein D is C(O)N(OH) or N(OH)C(O), pyrimidinone or pyridinone, each X independently of any other X is a saturated or partially unsaturated, substituted or unsubstituted linker comprising 8-11 atoms selected from any of N, C, O; R1 is alkyl, cycloalkyl, arene, or heteroarene, E is a saturated or partially unsaturated, substituted or unsubstituted chain comprising 1 - 50 atoms and R2 is a moiety capable of selectively binding to a biomolecule, or a nanoparticle. The invention further relates to complexes of the ligand, particularly radionuclides and their use in radioimmunotherapy and imaging.

  该发明涉及一般公式为R1 - D - X - D - X - D - X - D - E - R2的八齿配体，其中D为C(O)N(OH)或N(OH)C(O)，嘧啶酮或吡啶酮，每个X独立于其他X，是由N、C、O中的任意8-11个原子构成的饱和或部分不饱和、取代或未取代的连接基；R1为烷基、环烷基、芳烃或杂环烃；E为由1-50个原子构成的饱和或部分不饱和、取代或未取代链；R2为能够选择性结合生物分子或纳米颗粒的基团。该发明还涉及配体的络合物，特别是放射性同位素及其在放射免疫治疗和成像中的应用。